61070-20-0Relevant articles and documents
MITOCHONDRIA-TARGETING PEPTIDES
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Page/Page column 76; 77, (2019/07/19)
Disclosed are non-natural peptides useful for the treatment and prevention of ischemia-reperfusion injury (e.g., cardiac ischemia-reperfusion injury) or myocardial infarction.
Discovery of a low affinity thyrotropin-releasing hormone (TRH)-like peptide that exhibits potent inhibition of scopolamine-induced memory impairment in mice
Meena, Chhuttan L.,Ingole, Shubdha,Rajpoot, Satyendra,Thakur, Avinash,Nandekar, Prajwal P.,Sangamwar, Abhay T.,Sharma, Shyam S.,Jain, Rahul
, p. 56872 - 56884 (2015/07/15)
TRH-like peptides were synthesized in which the critical N-terminus residue l-pGlu was replaced with various heteroaromatic rings, and the central residue histidine with 1-alkyl-l-histidines. All synthesized TRH-like peptides were evaluated in vitro as agonists in HEK mTRH-R1 and HEK mTRH-R2 cell lines, an expressing receptor binding assay (IC50), and cell signaling assay (EC50). The analeptic potential of the synthesized peptides was evaluated in vivo by using the antagonism of a pentobarbital-induced sleeping time. The peptides 6a, 6c and 6e were found to activate TRH-R2 with potencies (EC50) of 0.002 μM, 0.28 μM and 0.049 μM, respectively. In contrast, for signaling activation of TRH-R1, the same peptides required higher concentration of 0.414 μM, 50 μM and 19.1 μM, respectively in the FLIPR assay. The results showed that these peptides were 207, 178 and 389-fold selective towards TRH-R2 receptor subtype. In the antagonism of a pentobarbital-induced sleeping time assay, peptide 6c showed a 58.5% reduction in sleeping time. The peptide 6c exhibited high stability in rat blood plasma, a superior effect on the scopolamine-induced cognition impairment mice model, safe effects on the cardiovascular system, and general behavior using a functional observation battery (FOB).
Formamides derived from N-methyl amino acids serve as new chiral organocatalysts in the enantioselective reduction of aromatic ketimines with trichlorosilane
Malkov, Andrei V.,Ston?ius, Sigitas,MacDougall, Kenneth N.,Mariani, Andrea,McGeoch, Grant D.,Ko?ovsky, Pavel
, p. 264 - 284 (2007/10/03)
Asymmetric reduction of N-aryl ketimines 1a-k, 43, and 45 with trichlorosilane can be catalyzed by new N-methyl l-amino acid-derived Lewis-basic organocatalysts, such as the valine-derived bisamide 3d (10 mol%), in toluene at room temperature with high enantioselectivity (≤92% ee). The structure-reactivity investigation shows that the product configuration is controlled by the nature of the side chain of the catalyst scaffold (e.g., i-Pr vs Me, as in 3d and 6e), so that catalysts of the same absolute configuration may induce the formation of the opposite enantiomers of the product. Arene-arene interactions between the catalyst and the incoming imine appear to be the prerequisite for asymmetric induction. This metal-free, organocatalytic protocol is competitive with the traditional, metal-catalyzed methodology.
Facile one-step synthesis of N-α-Boc-1-alkyl-l-histidines
Kaur, Navneet,Monga, Vikramdeep,Jain, Rahul
, p. 6883 - 6885 (2007/10/03)
A convenient one-step synthesis of N-α-Boc-1-alkyl-l-histidines 2a-f starting from Boc-l-histidine is described. N-α-Boc-l-Histidine upon direct τ(N-1) ring alkylation with various alkyl halides in the presence of sodium hydride in DMF or CH3CN easily afforded N-α-Boc-1-alkyl- l-histidines 2a-f. The reaction works equally well in either DMF or CH 3CN as solvent, however, CH3CN is preferred due to ease of reaction work-up.
